Top San Diego Seasonal & Special Occasions - page 2

Do something different with your time in San Diego by taking part in this private hands-on cigar rolling workshop. Don’t worry about bringing anything with you, as all tools and materials are provided. During your class, learn top tips from expert cigar rollers as well as fascinating insights on the history of the craft that most travelers usually miss out on.

An easy beach break with regular, predictable waves that don’t get too big, La Jolla Shores is one of California’s best destinations for learning to surf. Join an experienced instructor and no more than four other learners on a class that’s good for absolute beginners and intermediates alike. Your class includes your board and an Everyday California rash guard top, with full wetsuits available at an additional charge.

Combine history with wine tasting on this guided walking tour around San Diego’s Little Italy. Discover the area’s history in a fun way, with stops at three locations to sample unique wines from California and Italy. Enjoy Italian food samples, such as pizza, calamari and meatballs, at two of the three locations.

Throughout December, Flagship’s fleet of yachts set the stage for unforgettable holiday celebrations. Step aboard for a festive evening filled with twinkling lights, elegant decor, and warm hospitality. Whether it’s a romantic date, family gathering, or company party, December Nights Dinner Cruises blend fine dining with stunning San Diego Bay views for the ultimate seasonal experience.

Private wine tour to Temecula stopping off at a lovely winery in Fallbrook. Monserate Winery began with a desire to preserve the beauty and integrity of Gird Valley. For 56 years, the beautiful 116-acre property was a public golf course, dotted with 100-year-old oaks and towering sycamore trees. After falling on hard times, the golf course closed. We had a vision to revitalize the land and create something incredible that would also enrich the lives of the surrounding community, and thus, Monserate Winery was born. We have been hard at work to bring this vision to life since 2016 and have made a lot of progress. Today, Monserate’s San Diego county wineries boast breathtaking vineyards, tranquil lakes, and spectacular scenery. As we continue to grow and expand our operations, we stay true to our original vision. We then stop off at lovely Mount Palomar winery and also Wilson Creek in Temecula.

San Diego has a great beer scene, and a fun way to explore it is by riding in a motorcycle sidecar. This is a private tour, great for family members, partners, and more. Helmets, goggles, blankets and safety gear will be provided, so know you’ll be in safe hands. After this tour, the rest of the day is yours to do as you please.

Explore some of the best eats in the Gaslamp Quarter of San Diego—and learn insider facts and stories about its sordid past—on this two-in-one, small-group walking tour. Join an expert guide who has the inside scoop on the district's hopping restaurant and bar scene. Sample delicious dishes at several eateries, sip drinks, and learn about the neighborhood's past as a notorious red-light district.

Get ready for a bar-hopping adventure like no other as we celebrate in the heart of downtown San Diego! This is your chance to experience the best nightlife the city has to offer, with a curated lineup of vibrant venues and unforgettable experiences. Gather your friends and get ready to kick off the long weekend in style. We've handpicked the hottest bars in town, each offering unique vibes, signature drinks, and a lively atmosphere that will keep the party going all night long. Sip on creative cocktails and dance to the beats of top DJs as we begin the crawl at our first stop. Experience the electric energy and indulge in the incredible drink specials that will set the tone for an epic night of celebration. The fun continues as we hop from one buzzing venue to another, each offering its own distinct flavor and charm. Discover hidden gems, make new friends, and create memories that will last a lifetime.

Check out four of San Diego’s nightclubs with a guided tour, so the planning is done for you, and you just get to have fun and make some new friends and memories. Your guides will take you to The Onyx Room, Syrah Wine Parlor, Whiskey Girl, and Parq Nightclub, and entry is included in the price. Soak up the ambience and have a great night.

Step into the shadowy underbelly of San Diego’s Gaslamp District, where the city’s rowdy frontier and hushed prohibition days of the past collides with its glittering modern nightlife, and where more than a few restless spirits linger long after last call. On this 21+ Haunted Pub Crawl, you’ll raise a glass in some of the district’s most storied and spirited locations. Stop by the Montijo Building, once home to a furniture store with a chilling sideline in coffins and embalming. Pause outside The Fluxx Nightclub, where the music and lights conceal one of the Gaslamp’s darkest histories. Then, uncover the eerie legends of the Horton Grand Hotel, a Victorian masterpiece said to still host a guest who never truly checked out. This isn’t your average stroll through the Gaslamp - it’s an adults-only journey into the eerie, intoxicating history that shaped the district and the ghosts that refuse to be forgotten. Valid U.S. ID or passport required. Drinks not included.

Enjoy a day in wine country outside San Diego in Temecula. Your small group is chauffeured to Old Town from San Diego to start the day exploring the quaint town and its shops and galleries. From there, enjoy lunch and a tasting at a winery. After your picnic, tour more wineries, enjoying tastings, and learn about the wines as you go.

This is an all-inclusive private luxury day trip to Mexico's Valle de Guadalupe. The top wine destination in Mexico. The region grows everything from Syrah to Tempranillo. This wonderful valley has been dubbed "The Napa of Mexico". When taking this tour, you will not have to wait in the long border line! I have a special entry pass and crossing the border should take no more than 20 minutes! If you have Global Entry or SENTRI, please let me know!

5 hour private wine tasting tour of the wineries in North County San Diego. This is a very unique tour as most people head to Temecula. North County wineries are very good and produce some lovely wines. The tour itself will be approximately 3 hours the other 2 hours will be the drive time from downtown to Escondido and back to downtown and also the drive time between wineries. You will see some very picturesque scenery of the Mountains in North County and all the beautiful wineries along the way. It’s a very enjoyable tour.

For 7 to 14 people. Enjoy a unique family-style gondola cruise through the scenic canals and waterways of Coronado Cays. This 50-minute journey accommodates up to 14 passengers, making it perfect for groups seeking a relaxing and memorable experience on the water. Select wines, non-alcoholic beverages, and assorted chocolates are available for purchase to enhance your cruise. Reservations are required, ensuring a tailored experience for your group. - 50-minute gondola cruise through Coronado Cays canals - Perfect for groups of up to 14 passengers - Optional purchases include wines and chocolates - Reservations required For 7 people minimum up to 14 passengers. Small groups of 2 to 6 passengers should book the "Gondola Cruise through the Coronado Cays" package.

Explore the diverse and colorful sites of Hillcrest, home of San Diego’s largest LGBTQ community, on a hosted walking bar hopping experience. Unlock the ultimate Hillcrest experience with a bar crawl. Join the only bar crawl in town and enjoy free entrance and discounts to bars and clubs, VIP experiences, and shots. Meet new people and make the most of your time in San Diego. Start your night with an exclusive pre-party at our local bar. Meet your queens and get ready for a night of fun. Enjoy 5 venues, shots, and VIP entrances, and a pre-drink ticketed event. Head to 1010 University Ave, San Diego, CA 92103 (University Ave & 10th Ave). You will find us in the courtyard area between Ike´s Place and Nishiki Ramen. Get free entrance all night long and enjoy a free shots start your night. Get access to the biggest club in town and party until the early hours of the morning.

Pacific Beach Family Photo Fun – Capture Your Best Beach Memories! Make your San Diego trip unforgettable with a fun and relaxed family photo session on the stunning shores of Pacific Beach! Unlike traditional studio sessions, this experience captures real moments—laughter, playfulness, and the natural beauty of the ocean. Why Book This Experience? ✔ Authentic & Candid – No stiff posing, just natural smiles and joy! ✔ Scenic Backdrop – Golden sunsets, sandy toes, and ocean waves. ✔ Personalized & Fun – Bring a change of clothes for multiple looks! ✔ High-Quality Images – You’ll receive 20 professionally edited photos. Perfect for families, couples, and friend groups who want to cherish their time in San Diego forever. Book now and let’s create magic by the sea! ✨

Celebrate the season with a holiday-themed Underground Donut Tour in San Diego’s Little Italy! Over two festive hours, you’ll visit four hand-picked stops featuring the city’s most delicious seasonal donuts and pastries. Stroll past twinkling lights, decorated lampposts, and the charming holiday market while soaking in the joyful neighborhood vibe. We kick things off at Devil’s Dozen Donuts with rooftop views and devilishly good flavors. Then, it’s off to a cozy local bakery known for its festive sweets, followed by The Donut Bar—famous for outrageous creations like peppermint, red velvet, and gingerbread. Finally, wind down at a local coffee roastery with a fresh brew to pair with your treats. This tour blends holiday cheer, waterfront charm, and sweet bites into a delightful winter experience. If you love donuts, lights, and holiday magic, this tour is your perfect seasonal outing. Book now and make some sweet memories!

Celebrate the magic of the season on the water with a Christmas Day Premier Brunch Cruise in San Diego. You and your guests will enjoy a holiday brunch buffet freshly prepared by our chef, full bar service, and City Cruises’ distinctive hospitality. While onboard, experience exceptional views of San Diego’s iconic skyline and waterfront, entertainment, and festive décor. Our team will happily take care of the details, leaving you to celebrate the holidays on the San Diego Bay with your friends and family. Happy Holidays!

Hit the bars in Pacific Beach with a fun loving group when you book this group bar tour in San Diego. You’ll have plenty of friends ready to party with you. Your guide will take you to some of the best bars in the area, and you’ll get exclusive discounts on drinks at each location. Have a great night out with a group of fun adults.

Keep your holiday merry and bright with a Christmas Eve Premier Brunch Cruise departing from San Diego. Featuring festive decor and a delicious meal, your Christmas on the water is sure to be a gift to yourself and your loved ones. Deck the halls with limited-time holiday entertainment and a festive retreat from land.

Capture unforgettable moments with a flying dress photoshoot designed for ladies, groups, or couples. Choose from a variety of stunning locations that best suit your style and vision, making each shoot uniquely yours. This experience is perfect for celebrating special occasions such as birthdays, engagements, vacations, or maternity. Create lasting memories while feeling empowered in beautiful, flowing dresses that dance in the wind, enhancing the magic of your photos. Couples and group discounts can be discussed!

Discover San Diego’s highlight North Coast craft breweries—and enjoy a fun-filled and personalized way to explore—on this small-group, half-day tour. Following pickup, travel in a vintage VW Vanagon, with drinks and snacks provided. You’ll visit three area craft breweries, where you can indulge in a generous array of samples, relax, and learn more about the brewing process.

Discover Coronado Island from a whole new perspective on this Sunset and Night‑Glow Clear Kayaking Tour, a unique small‑group experience that lets you paddle across calm San Diego waters in luxury transparent kayaks illuminated with vibrant LED lights. As the sun dips behind the skyline, enjoy sweeping views of downtown San Diego and watch the city transform into a glowing waterfront backdrop. Glide across the bay in clear, see‑through kayaks, offering an immersive look at the water below by day and a colorful light display by night. Ideal for couples, families, and groups, this 90‑minute experience blends relaxation, sightseeing, and a touch of adventure. Your guides lead the group safely along scenic routes while you take in the sunset and the illuminated skyline.

Bring the magic of the season to life with a dinner cruise departing from San Diego. With cruises featuring festive décor and a delicious meal, celebrating Christmas on the San Diego Bay with your friends and family will keep your holiday merry and bright!